Interesting. I have a bunch of private notes on the subject from when I was last playing with startup ideas. The biggest hurdle I kept hitting was differentiating the startup within the calendar space, because it is a pretty well saturated space with a lot of entrenched players. (Similarly as bad as the Mail space, if not worse, just as we've seen several apps exit these past couple of weeks. Though some of those efforts have exited well for the startup founders, so that's an issue more for the overly conservative "local" VCs I was curious if I could get to invest, when I was putting my notes together…)

The partial pivot to automating web meetings is a neat idea, but the immediate concern I would see there is that now you're fighting two fairly heavily entrenched spaces, calendars and web meetings. Twice the battle fronts might mean twice the opportunities to exit, but it also might mean twice the opportunities to be out-competed/exhausted?